KR102076958B1 - 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 - Google Patents

헤테로고리 화합물 및 이를 이용한 유기 발광 소자 Download PDF

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Publication number: KR102076958B1
Authority: KR; South Korea
Prior art keywords: group; substituted; light emitting; unsubstituted; organic light
Prior art date: 2019-06-24

Application number

KR1020190075259A

Other languages

English (en)

Korean (ko)

Inventor

김지운

정유준

이남진

정원장

모준태

Original Assignee

엘티소재주식회사

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2019-06-24

Filing date

2019-06-24

Publication date

2020-02-13

2019-06-24 Application filed by 엘티소재주식회사 filed Critical 엘티소재주식회사

2019-06-24 Priority to KR1020190075259A priority Critical patent/KR102076958B1/ko

2020-02-13 Application granted granted Critical

2020-02-13 Publication of KR102076958B1 publication Critical patent/KR102076958B1/ko

2020-06-10 Priority to EP20179205.8A priority patent/EP3757095A3/en

2020-06-18 Priority to TW109120492A priority patent/TWI811551B/zh

2020-06-23 Priority to US16/909,618 priority patent/US11812623B2/en

2020-06-23 Priority to CN202010579987.2A priority patent/CN112125872B/zh

2020-06-24 Priority to JP2020108800A priority patent/JP7226817B2/ja

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238000004506 ultrasonic cleaning Methods 0.000 description 1
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GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1

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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- H01L51/0073—
- H01L51/5012—
- H01L51/5056—
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/19—Tandem OLEDs
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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KR1020190075259A 2019-06-24 2019-06-24 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 KR102076958B1 (ko)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPWO2022009999A1 (zh) *	2020-11-05	2022-01-13
KR20220031422A (ko) *	2020-09-04	2022-03-11	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102374470B1 (ko) *	2021-07-21	2022-03-15	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN114671835A (zh) *	2020-12-24	2022-06-28	Lt素材株式会社	杂环化合物、包含其的有机发光器件及组合物及用于制造所述有机发光器件的方法
WO2022250244A1 (ko) *	2021-05-24	2022-12-01	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2023096225A1 (ko) *	2021-11-29	2023-06-01	엘티소재주식회사	헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물
KR102685637B1 (ko) *	2020-12-24	2024-07-19	엘티소재주식회사	헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR102326512B1 (ko) *	2020-01-14	2021-11-16	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20210138823A (ko) *	2020-05-11	2021-11-22	삼성디스플레이 주식회사	유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물
WO2022181072A1 (ja) *	2021-02-26	2022-09-01	出光興産株式会社	有機エレクトロルミネッセンス素子、及び電子機器
KR102574328B1 (ko) *	2021-06-08	2023-09-06	엘티소재주식회사	헤테로고리 화합물, 및 이를 포함하는 유기 발광 소자
KR102611370B1 (ko) *	2021-08-25	2023-12-08	엘티소재주식회사	헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR102522432B1 (ko) *	2021-12-20	2023-04-19	삼성디스플레이 주식회사	발광 소자 및 발광 소자용 아민 화합물
WO2023190597A1 (ja) *	2022-03-29	2023-10-05	出光興産株式会社	有機エレクトロルミネッセンス素子及び電子機器

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4356429A (en)	1980-07-17	1982-10-26	Eastman Kodak Company	Organic electroluminescent cell
CN104650029A (zh) *	2014-12-26	2015-05-27	北京鼎材科技有限公司	一种稠杂环芳烃衍生物及其应用
KR20150145033A (ko) *	2014-06-18	2015-12-29	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR101789998B1 (ko) *	2016-05-26	2017-10-25	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
JP2018156721A (ja) *	2015-07-14	2018-10-04	出光興産株式会社	有機エレクトロルミネッセンス素子および電子機器

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104884444B (zh)	2012-12-26	2018-07-03	出光兴产株式会社	含氧稠环胺化合物、含硫稠环胺化合物及有机电致发光元件
KR20150146033A (ko)	2014-06-20	2015-12-31	김현정	가습장치
KR102329807B1 (ko) *	2014-11-05	2021-11-22	덕산네오룩스 주식회사	유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
KR102293436B1 (ko) *	2014-11-19	2021-08-25	덕산네오룩스 주식회사	유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
US10312449B2 (en) *	2015-05-27	2019-06-04	Samsung Display Co., Ltd.	Organic light-emitting device
KR101907739B1 (ko)	2015-06-15	2018-10-12	주식회사 엘지화학	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
ES2914681T3 (es)	2015-07-02	2022-06-15	Janssen Sciences Ireland Unlimited Co	Compuestos antibacterianos
KR101984244B1 (ko) *	2015-09-09	2019-05-30	삼성에스디아이 주식회사	유기 화합물, 유기 광전자 소자 및 표시 장치
WO2017090919A1 (ko)	2015-11-26	2017-06-01	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102617840B1 (ko)	2015-11-26	2023-12-26	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102111829B1 (ko)	2016-02-17	2020-05-15	주식회사 엘지화학	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
US10998502B2 (en) *	2016-06-28	2021-05-04	Duk San Neolux Co., Ltd.	Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN106565705B (zh) *	2016-10-26	2019-06-25	北京绿人科技有限责任公司	一种有机化合物及其在电致发光器件中的应用
KR102146792B1 (ko)	2017-08-01	2020-08-21	삼성에스디아이 주식회사	유기 광전자 소자용 화합물, 유기 광전자 소자 및 표시 장치
KR102443233B1 (ko)	2017-09-22	2022-09-15	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102418440B1 (ko)	2017-09-29	2022-07-07	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2019066250A1 (ko) *	2017-09-29	2019-04-04	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2019066242A1 (ko)	2017-09-29	2019-04-04	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102611877B1 (ko)	2017-12-21	2023-12-08	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2019124903A1 (ko) *	2017-12-21	2019-06-27	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102603517B1 (ko)	2017-12-21	2023-11-17	코웨이 주식회사	냉수 및 얼음 생성 장치 및 이의 제어 방법

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- 2019-06-24 KR KR1020190075259A patent/KR102076958B1/ko active IP Right Grant
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Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4356429A (en)	1980-07-17	1982-10-26	Eastman Kodak Company	Organic electroluminescent cell
KR20150145033A (ko) *	2014-06-18	2015-12-29	덕산네오룩스 주식회사	유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN104650029A (zh) *	2014-12-26	2015-05-27	北京鼎材科技有限公司	一种稠杂环芳烃衍生物及其应用
JP2018156721A (ja) *	2015-07-14	2018-10-04	出光興産株式会社	有機エレクトロルミネッセンス素子および電子機器
KR101789998B1 (ko) *	2016-05-26	2017-10-25	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20220031422A (ko) *	2020-09-04	2022-03-11	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102428785B1 (ko)	2020-09-04	2022-08-03	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20230104066A (ko)	2020-11-05	2023-07-07	이데미쓰 고산 가부시키가이샤	화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
JP7525580B2 (ja)	2020-11-05	2024-07-30	出光興産株式会社	化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
US12012389B2 (en)	2020-11-05	2024-06-18	Idemitsu Kosan Co., Ltd.	Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
JP7196363B2 (ja)	2020-11-05	2022-12-26	出光興産株式会社	化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
JPWO2022009999A1 (zh) *	2020-11-05	2022-01-13
US11795155B2 (en)	2020-11-05	2023-10-24	Idemitsu Kosan Co., Ltd.	Compound having naphthobenzofuranyl structure, material for organic electroluminescence device, organic electroluminescence device, and electronic instrument
CN114671835A (zh) *	2020-12-24	2022-06-28	Lt素材株式会社	杂环化合物、包含其的有机发光器件及组合物及用于制造所述有机发光器件的方法
EP4019505A1 (en) *	2020-12-24	2022-06-29	LT Materials Co., Ltd.	Heterocyclic compound, organic light emitting device comprising the same, method for manufacturing the same and composition for organic material layer of organic light emitting device
JP2022101491A (ja) *	2020-12-24	2022-07-06	エルティー・マテリアルズ・カンパニー・リミテッド	ヘテロ環化合物、これを含む有機発光素子、その製造方法および有機物層用組成物
KR102685637B1 (ko) *	2020-12-24	2024-07-19	엘티소재주식회사	헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물
KR102599516B1 (ko)	2021-05-24	2023-11-09	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20220158892A (ko) *	2021-05-24	2022-12-02	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2022250244A1 (ko) *	2021-05-24	2022-12-01	엘티소재주식회사	헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20230070197A (ko) *	2021-07-21	2023-05-22	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
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KR102627130B1 (ko)	2021-07-21	2024-01-23	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102374470B1 (ko) *	2021-07-21	2022-03-15	덕산네오룩스 주식회사	유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2023096225A1 (ko) *	2021-11-29	2023-06-01	엘티소재주식회사	헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물

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